On the properties of bit string-based measures of chemical similarity
On the properties of bit string-based measures of chemical similarity
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DOI：
10.1021/ci970437z
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发表时间：
1998-05-01
期刊：
影响因子：
--
通讯作者：
Flower, DR
中科院分区：
文献类型：
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作者：
Flower, DR
随着人们对数据库检索和化合物选择的兴趣的增长，化学相似性的量化已经成为一个具有强烈实践和理论兴趣的领域。测量化学相似性的最广泛使用的方法之一是基于将分子内的片段映射为二进制字符串中的位。我们提出的经验结果表明，位串提供了分子大小、形状和全局相似性的非直观编码。其他结果（这次是统计性质的）表明，观察到的基于位字符串的搜索行为具有很大的非特定成分。在此基础上，我们质疑基于位串的相似性方法是否具有定量化学距离测量或度量所需的所有特征，并建议在某些情况下，它们可能不是搜索或分离化学结构的最合适工具。
With the growth of interest in database searching and compound selection, the quantification of chemical similarity has become an area of intense practical and theoretical interest. One of the most widely used methods of measuring chemical similarity is based on mapping fragments within a molecule as bits within a binary string. We present empirical results which suggest that bit strings provide a nonintuitive encoding of molecular size, shape, and global similarity. Other results, this time statistical in nature, suggest that the observed behavior of bit string-based searches have a large nonspecific component. On this basis, we question whether bit string-based similarity methods possess all the features desirable in a quantitative chemical distance measure or metric and suggest that there are instances when they may not be the most appropriate tool for searching or segregating chemical structures.